Reacción #2186184

Ecuación de reacción

compound ( b66 )

3-chloro-2-fluoro-4-methoxy-4′-propylbiphenyl

boron tribromide

water

→

3-chloro-2-fluoro-4′-propylbiphenyl-4-ol

Rendimiento 86.2%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   workup.WAITthe mixture was left at rest
3. 3
   Otroto separate into an organic layer
4. 4
   Extracciónby extracting to the organic layer
5. 5
   LavadoThe resulting organic layer was washed with a sodium chloride aqueous solution in three times
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   Otroto obtain a residue
9. 9
   Otro19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume)

Procedimiento

22.0 g of the compound (b66) was dissolved in 200 mL of methylene chloride. 23.7 g of boron tribromide was added dropwise to the resulting solution in a temperature range of −27 to −20° C., and the temperature of the solution was gradually increased to room temperature, followed by stirring overnight. The resulting reaction mixture was poured slowly to 300 mL of iced water, and the mixture was left at rest to separate into an organic layer and an aqueous layer, followed by extracting to the organic layer. The resulting organic layer was washed with a sodium chloride aqueous solution in three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a residue. The residue was a yellowish solid. 19.7 g of the residue was purified by recrystallization from a mixed solvent of heptane and toluene (heptane/toluene=2/1 by volume) to obtain 18.0 g of 3-chloro-2-fluoro-4′-propylbiphenyl-4-ol (b67). The resulting compound (b67) was a white solid.

Fuente